Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/06—Peri-condensed systems
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
  • G03G5/0601—Acyclic or carbocyclic compounds
  • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
  • G03G5/0622—Heterocyclic compounds
  • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
  • G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
  • G03G5/0651—Heterocyclic compounds containing two or more hetero rings in the same ring system containing four relevant rings

Definitions

• the present invention relates to photoconductive compositions containing cyclic bis-dicarboximide sensitizers.
• Photoconductive compositions are employed in well-known imaging processes involving, for example, charging, imagewise exposure to actinic radiation and development to form a toner image on the composition.
• the composition must be adequately sensitive to light so that inordinate degrees of exposure are not required.
• Efforts to improve the sensitivity of the photoconductive composition have led to a variety of so-called sensitizing compounds which increase the response of the photoconductive composition both in the spectral region where it is intrinsically sensitive and in other spectral regions. While many sensitizing compounds are currently known, continuing research is underway to find new materials.
• sensitivity below 400 nm only and nonpersistent conductivity are highly desirable. (400 nm represents the approximate spectral wavelength of transition between visible and nonvisible light; persistent conductivity refers to the lingering conductivity of some materials in exposed regions.) Exclusive sensitivity below 400 nm permits development of the photoconductive composition in visible light. It also facilitates use of the photoconductive composition in second-stage operations such as contact printing by transmitting light above 400 nm through the composition onto a second material which is sensitive to the transmitted light.
• Nonpersistent conductivity is important if a photoconductive composition is to be cycled through a charge-expose-develop sequence a number of times in rapid succession. If the photoconductive composition is persistent, unwanted images from preceding sequences will contaminate the image desired.
• R 1 and R 2 which may be the same or different, represent aryl, such as phenyl or naphthyl, or aryl substituted with alkyl, alkoxy, perfluoroalkyl or perfluoroalkoxy groups having 2 to 20 alkyl carbon atoms; sulfonyl; sulfone; sulfonamide; nitrile; or nitro groups;
• R 3 , R 4 , R 5 and R 6 which may be the same or different, represent hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, or halogen;
• n 0 to 3.
• R 1 and R 2 in Formula I are phenyl or phenyl substituted with alkyl, alkoxy or perfluoralkyl, and R 3 , R 4 , R 5 and R 6 are hydrogen.
• the above photoconductive composition is a singlephase homogeneous mixture of the photoconductor, dicarboximide sensitizer and binder, if a binder is desired.
• the components of the composition are selected so as to be rendered soluble in common coating solvents such as halogenated hydrocarbon liquids.
• the solubility of the Strcuture I dicarboximide sensitizer in a coating solvent is at least 0.25 percent by weight of the resulting solution, and most preferably at least 1 percent by weight of the solution.
• Homogeneous compositions of the present invention are preferably prepared by coating from halogenated hydrocarbon liquids such as 1,2-dichloroethane, 1,1,2-trichloropropane and 1,1,2,2-tetrachloroethane.
• halogenated hydrocarbon liquids such as 1,2-dichloroethane, 1,1,2-trichloropropane and 1,1,2,2-tetrachloroethane.
• Representative 1,4,5,8-naphthalene bis-dicarboximides employed in the defined composition include the compounds listed in Table 1.
• the amount of dicarboximide employed can vary widely in accordance with the degree of sensitization desired. Effective amounts of the sensitizer represented by Structure I can vary widely in order to increase the speed of the photoconductive composition relative to compositions without the sensitizer of Structure I. The optimum concentration in any given case will vary with the specific photoconductor and sensitizing compound used. Substantial speed gains can be obtained where a sensitizer according to Structure I is added in a concentration range from about 0.0001 to about 30 percent based on the weight of the composition on a dry basis. A preferred sensitizer concentration range is from about 0.005 to about 5.0 percent.
• dicarboximide sensitizers used in this invention are effective for enhancing the electrophotosensitivity of a wide variety of photoconductors.
• Representative photoconductors useful in compositions containing the present sensitizers are described below:
• arylamine photoconductors including substituted and unsubstituted arylamines, diarylamines, nonpolymeric triarylamines and polymeric triarylamines such as those described in U.S. Pat. No. 3,240,597 by Fox issued Mar. 15, 1966, and U.S. Pat. No. 3,180,730 by Klupfel et al issued Apr. 27, 1965;
• triarylamines in which at least one of the aryl radicals is substituted by either a vinyl radical or a vinylene radical having at least one active hydrogen-containing group, as described in U.S. Pat. No. 3,567,450 by Brantly et al issued Mar. 2, 1971;
• arylalkane leuco base photoconductors are the principal photoconductive constituents. Such preferred compositions are advantageously nonpersistently conductive and sensitive to radiation below 400 nm, but substantially insensitive to radiation above 400 nm.
• Arylalkane leuco base photoconductors are disclosed, for example, in U.S. Pat. No. 3,542,547 above and bear the structure: ##STR7## wherein:
• each of R and R' is selected from the group consisting of hydrogen, alkyl and aralkyl having 1 to 4 carbon atoms in the alkyl group;
• each of X' and X" is selected from the group consisting of alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, hydroxyl and halogen;
• each of Y' and Y" is selected from the group consisting of alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, hydroxyl, halogen and hydrogen; and
• each of A and B is:
• aryl such as phenyl, ⁇ -naphthyl, ⁇ -naphthyl, 9-anthryl and substituted derivatives thereof wherein the substituent is dialkylamino, alkylamino, amino, alkyl, alkoxy, hydroxyl or halogen;
• an aliphatic alkyl group having 1-18 carbon atoms e.g., methyl, ethyl, propyl, butyl, isobutyl, octyl, dodecyl, etc., including a substituted alkyl group having 1-18 carbon atoms;
• a cycloalkyl group having 4-8 carbon atoms in the cyclic nucleus e.g., cyclobutyl, cyclohexyl, cyclopentyl, etc., including a substituted cycloalkyl group; or
• a cycloalkenyl group having 4-8 carbon atoms in the cyclic nucleus e.g., cyclohex-3-enyl, cyclopent-3-enyl, cyclobut-2-enyl, cyclohex-2-enyl, etc., including a substituted cycloalkenyl group.
• compositions of the present invention comprise crystallization-inhibiting mixtures of two or more of the arylalkane leuco base photoconductors as disclosed in U.S. Pat. No. 4,301,226 issued Nov. 17, 1981, to L. E. Contois et al.
• a preferred crystallization-inhibiting mixture comprises three arylmethane photoconductors: bis(4-N,N-diethylamino-2-methylphenyl)-4-methylphenylmethane, 1,1-bis(4-N,N-diethylamino-2-methylphenyl)-2-methylpropane and 4,4'-bis(diethylamino)-2,2'-dimethyltriphenylmethane.
• the total amount of photoconductor in the defined composition may vary widely, but preferably ranges from about 5 to about 40 weight percent based on the solvent-free weight of the layer.
• compositions of the present invention are incorporated into an electrically insulating binder and coated as photoconductive layers on an electrically conductive support to form a photoconductive element.
• the elements so formed are employed in electrophotographic processes to form toned images in a conventional manner.
• Preferred electrically insulating binders for use in preparing the photoconductive layers are film-forming, hydrophobic polymeric binders having fairly high dielectric strength.
• Materials of this type comprise styrene-butadiene copolymers; silicone resins; styrene-alkyd resins; silicone-alkyd resins; soya-alkyld resins; poly(vinyl chloride); poly(vinylidene chloride); vinylidene chloride-acrylonitrile copolymers; poly(vinyl acetate); vinyl acetate-vinyl chloride copolymers; poly(vinyl acetals) such as poly(vinyl butyral); polyacrylic and polymethacrylic esters such as poly(methyl methacrylate), poly(n-butyl methacrylate), poly(isobutyl methacrylate); polystyrene; nitrated polystyrene; polymethylstyrene; isobutylene poly
• Suitable supporting materials for the photoconductive layers of the present invention can include any electrically conducting support.
• Examples include conducting papers, aluminum-paper laminate, metal foils such as aluminum and zinc foils; metal plates such as aluminum, copper, zinc, brass and galvanized plates, vapor-deposited metal layer (silver, nickel, aluminum) on conventional film supports such as cellulose acetate, poly(ethylene terephthalate), polystyrene and the like.
• a useful conducting support can be prepared by coating a transparent film support such as poly(ethylene terephthalate) with a layer containing a semiconductor dispersed in a resin.
• a suitable conducting coating can be prepared from the sodium salt of a carboxyester lactone of a maleic anhydride-vinyl acetate copolymer or cuprous iodide or the like.
• a solution was prepared with 2 g of Lexan 145TM binder (a poly[4,4'-isopropylidenediphenylene carbonate] available from General Electric Company), 0.8 g of Compound I of Table 2 and 0.029 g of Compound A, Table 1, in 20 mL of methylene chloride.
• the solution was heated gently for about 1 hr and was then coated at 26° C. to a wet thickness of 100 ⁇ m on the barrier layer of a conductive film support.
• the support included a cellulose nitrate barrier layer overlying a cuprous iodide conducting layer on a polyethylene terephthalate substrate.
• the film was placed in a drying oven overnight at 65° C. to produce a dry, homogeneous photoconductive layer. The dry thickness of the film was 8 ⁇ m.
• the coated photoconductive layer had absorption peaks at 360 nm (optical density, O.D., of 0.51) and 380 nm (O.D. of 0.43). There was a sharp cutoff in the absorption at 400 nm. (At 400 nm, the O.D. was 0.1, and at 416 nm, the O.D. was 0.02). The element was clear and appeared colorless to the naked eye. The element exhibited substantially no persistent conductivity.
• the film absorbed 63% of the incident light.
• the dye absorbed 58% of the incident lihgt.
• the element was nonpersistent.

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• General Physics & Mathematics (AREA)
• Health & Medical Sciences (AREA)
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• Photoreceptors In Electrophotography (AREA)

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Cited By (34)

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• 1983
  • 1983-02-22 US US06/468,726 patent/US4442193A/en not_active Expired - Lifetime
• 1984
  • 1984-01-25 CA CA000446045A patent/CA1212855A/en not_active Expired
  • 1984-02-20 EP EP84301067A patent/EP0119755B1/de not_active Expired
  • 1984-02-20 DE DE8484301067T patent/DE3467939D1/de not_active Expired
  • 1984-02-21 JP JP59031313A patent/JPS59164559A/ja active Granted

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